Medical glue for trauma, preparation method and application thereof

By adjusting the composition and ratio of α-cyanoacrylate medical adhesives, the problems of excessively fast polymerization speed, excessive bonding strength, and difficult operation were solved, enabling rapid and safe bonding of medical adhesives in outdoor environments, making them suitable for skin protection during outdoor sports.

CN116549709BActive Publication Date: 2025-10-28FUALIE SCI & TECH DEVING BEIJING
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Patent Information

Application Number
CN202310578942.7
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2023-05-22
Publication Date
2025-10-28
Estimated Expiration
2043-05-22

AI Technical Summary

Technical Problem

Existing α-cyanoacrylate medical adhesives polymerize too quickly in outdoor environments, have excessively high bonding strength, are prone to flowing, and are difficult to handle, making it difficult to meet the bonding requirements of different tissue sites.

Method used

The composition of medical adhesives was optimized by adjusting the proportions of alkyl α-cyanoacrylate, plasticizer, and thickener, including the weight ratio of n-butyl α-cyanoacrylate and n-octyl α-cyanoacrylate, as well as the proportions of plasticizers diethyl adipate, diethylene glycol dibenzoate, and polyoxypropylene aryl ether. Combined with the use of styrene copolymer and nitrile rubber, polymerization time and viscosity were controlled to improve flexibility and adhesion.

Benefits of technology

It enables rapid, safe, and operable bonding of medical adhesives in outdoor environments, reduces polymerization heat, and improves tensile strength and peel performance, making it suitable for skin protection in outdoor sports such as rock climbing.

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Abstract

This invention relates to the field of biomaterials technology, particularly to the field of IPC C07C253, and more specifically, to a medical adhesive for external wounds, its preparation method, and its application. By weight, the components include: 80-120 parts of alkyl α-cyanoacrylate, 0.1-2 parts of polymerization inhibitor, 5-15 parts of plasticizer, and 3-12 parts of thickener. The alkyl α-cyanoacrylate includes n-butyl α-cyanoacrylate and n-octyl α-cyanoacrylate, with a weight ratio of 2:(0.5-1.5), which improves the tensile strength of the medical adhesive. The plasticizer includes diethyl adipate, diethylene glycol dibenzoate, and polyoxypropylene aryl ether, with a weight ratio of 1:(0.5-1):(1-1.8), which balances the tensile and peel properties of the medical adhesive.
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Description

Technical Field

[0001] This invention relates to the field of biomaterials, particularly to the field of IPC C07C253, and more specifically, to a medical adhesive for trauma, its preparation method, and its application. Background Technology

[0002] Skin pressure-sensitive adhesives are composed of elastomers and tackifying resins, and come in many varieties. Currently, the medical adhesives available in China for skin surfaces are mainly butyl α-cyanoacrylate and octyl α-cyanoacrylate. However, to meet the bonding requirements of different tissue sites, the required bonding strength, bonding speed, curing time, and viscosity of each adhesive vary. Currently, α-cyanoacrylate has defects such as excessively fast polymerization speed, excessively high bonding strength, easy flow, and difficulty in operation, making it unsuitable for rapid and safe wound treatment in outdoor environments.

[0003] CN 111714685 A discloses a method for preparing medical adhesive using alkyl cyanoacrylate monomer. The medical adhesive prepared using alkyl cyanoacrylate monomer, formaldehyde, piperidine catalyst, sodium dodecyl sulfate, phosphoric acid alkaline catalyst, purified water, tricresyl phosphate plasticizer, hydroquinone polymerization inhibitor, ethyl cyanoacetate, isobutanol, phthalate, and acidic catalyst can improve the compatibility of the medical adhesive while reducing its adhesion, but it does not improve the problem of fast polymerization time and easy breakage of the adhesive layer. Summary of the Invention

[0004] The first aspect of the present invention provides a medical adhesive for external injuries, comprising, by weight: 80-120 parts of alkyl α-cyanoacrylate, 0.1-2 parts of polymerization inhibitor, 5-15 parts of plasticizer, and 3-12 parts of thickener.

[0005] The alkyl α-cyanoacrylate includes n-butyl α-cyanoacrylate and n-octyl α-cyanoacrylate, wherein the weight ratio of n-butyl α-cyanoacrylate to n-octyl α-cyanoacrylate is 2:(0.5-1.5).

[0006] Preferably, the weight ratio of α-butyl cyanoacrylate to α-octyl cyanoacrylate is 2:(0.7-1.4).

[0007] More preferably, the weight ratio of α-butyl cyanoacrylate to α-octyl cyanoacrylate is 2:0.8.

[0008] The plasticizer includes at least one of trimethyl trimellitate, diethylene benzoate, diethyl malonate, triethyl O-acetyl citrate, benzyl butyl phthalate, dipropylene glycol dibenzoate, diethyl adipate, tributyl O-acetyl citrate, dimethyl sebacate, and aryl ether.

[0009] The applicant's research found that the plasticizer includes diethyl adipate, diethylene glycol dibenzoate, and polyoxypropylene aryl ether, with a weight ratio of 1:(0.5-1):(1-1.8). This balances the tensile and peel properties of the medical adhesive. During the polymerization process of the medical adhesive, diethyl adipate molecules insert into the polymer molecular chain, weakening the stress between the polymer molecular chains. However, excessive diethyl adipate reduces the tensile strength of the polymer. Adding a certain amount of diethylene glycol dibenzoate, with the presence of the rigid benzene ring group, can improve the tensile strength of the medical adhesive, but it can easily lead to excessive peel strength, causing skin adhesion during use. The addition of polyoxypropylene aryl ether can further balance the tensile and peel properties of the medical adhesive, possibly by improving the compatibility between the plasticizer and alkyl α-cyanoacrylate, and improving the uniformity of curing.

[0010] Preferably, the plasticizer includes diethyl adipate, diethylene glycol dibenzoate, and polyoxypropylene aryl ether, wherein the weight ratio of diethyl adipate, diethylene glycol dibenzoate, and polyoxypropylene aryl ether is 1:(0.5-1):(1-1.8).

[0011] More preferably, the plasticizer includes diethyl adipate, diethylene glycol dibenzoate, and polyoxypropylene aryl ether, wherein the weight ratio of diethyl adipate, diethylene glycol dibenzoate, and polyoxypropylene aryl ether is 1:0.5:1.2.

[0012] The thickener includes at least one of methacrylate polymers, polyvinyl acetal, styrene copolymers, and nitrile rubber.

[0013] Preferably, the thickener comprises styrene copolymer and nitrile rubber, wherein the weight ratio of styrene copolymer to nitrile rubber is 1:(0.2-0.6).

[0014] More preferably, the thickener comprises styrene copolymer and nitrile rubber, wherein the weight ratio of styrene copolymer to nitrile rubber is 1:0.5.

[0015] Preferably, the styrene copolymer is SEPS, model: G1701MU, purchased from Boruida (Dongguan) New Materials Co., Ltd.

[0016] Preferably, the nitrile rubber includes liquid nitrile rubber, model: LNBR26, purchased from Greenlink (Jining) Chemical Technology Co., Ltd.

[0017] The polymerization inhibitor includes at least one of sulfur dioxide, trifluoroacetic acid, and hydroquinone.

[0018] Preferably, the polymerization inhibitor includes sulfur dioxide.

[0019] The weight ratio of the plasticizer to the thickener is 1:(0.6-1.1).

[0020] Preferably, the weight ratio of the plasticizer to the thickener is 1:0.75.

[0021] The weight ratio of the alkyl α-cyanoacrylate to the plasticizer is 20:(1-3).

[0022] Preferably, the weight ratio of the α-cyanoacrylate alkyl ester to the plasticizer is 20:2.4.

[0023] A second aspect of this invention provides a method for preparing medical adhesive for external wounds, comprising the following steps:

[0024] Step 1: Sterilize the polymer inhibitor, plasticizer, and thickener after mixing them thoroughly.

[0025] Step 2: Add the product obtained in Step 1 to α-cyanoacrylate alkyl ester and stir until homogeneous to obtain the final product.

[0026] The third aspect of this invention provides an application of medical adhesive for external wounds, used for skin surface protection during outdoor sports.

[0027] Preferably, the outdoor sport includes at least one of hiking, mountaineering, and rock climbing.

[0028] More preferably, the outdoor sport includes rock climbing.

[0029] Beneficial effects:

[0030] 1. The alkyl α-cyanoacrylate includes n-butyl α-cyanoacrylate and n-octyl α-cyanoacrylate, wherein the weight ratio of n-butyl α-cyanoacrylate to n-octyl α-cyanoacrylate is 2:(0.5-1.5), which can improve the tensile strength of medical adhesive.

[0031] 2. The plasticizer includes diethyl adipate, diethylene glycol dibenzoate, and polyoxypropylene aryl ether, wherein the weight ratio of diethyl adipate, diethylene glycol dibenzoate, and polyoxypropylene aryl ether is 1:(0.5-1):(1-1.8), which can balance the tensile and peel properties of medical adhesive.

[0032] 3. The thickener includes styrene copolymer and nitrile rubber, wherein the weight ratio of styrene copolymer to nitrile rubber is 1:(0.2-0.6), which can reduce the precipitation of plasticizer and at the same time give the medical adhesive a certain viscosity, making it convenient for outdoor application of medicine.

[0033] 4. The weight ratio of the plasticizer to the thickener is 1:(0.6-1.1), and the polymerization time of the medical adhesive reaches s, which effectively reduces the heat of polymerization and improves the user experience.

[0034] 5. The weight ratio of the α-cyanoacrylate alkyl ester to the plasticizer is 20:(1-3). The medical adhesive has excellent flexibility and can be used in outdoor sports such as rock climbing. It can quickly bond joints and is not prone to adhesive layer damage. Detailed Implementation

[0035] Example 1

[0036] A medical adhesive for external wounds, by weight, comprises: 100 parts of alkyl α-cyanoacrylate, 0.2 parts of polymerization inhibitor, 12 parts of plasticizer, and 9 parts of thickener.

[0037] The alkyl α-cyanoacrylate is butyl α-cyanoacrylate and octyl α-cyanoacrylate, and the weight ratio of butyl α-cyanoacrylate to octyl α-cyanoacrylate is 2:0.8.

[0038] The plasticizer is diethyl adipate, diethylene glycol dibenzoate, and polyoxypropylene aryl ether, and the weight ratio of diethyl adipate, diethylene glycol dibenzoate, and polyoxypropylene aryl ether is 1:0.5:1.2.

[0039] The thickener is a styrene copolymer and acrylonitrile rubber, wherein the weight ratio of the styrene copolymer to the acrylonitrile rubber is 1:0.5.

[0040] The styrene copolymer is SEPS, model: G1701MU, purchased from Boruida (Dongguan) New Materials Co., Ltd.

[0041] The nitrile rubber is liquid nitrile rubber, model: LNBR26, purchased from Greenlink (Jining) Chemical Technology Co., Ltd.

[0042] The polymerization inhibitor is sulfur dioxide.

[0043] A method for preparing a medical adhesive for external wounds includes the following steps:

[0044] Step 1: Sterilize the polymer inhibitor, plasticizer, and thickener after mixing them thoroughly.

[0045] Step 2: Add the product obtained in Step 1 to α-cyanoacrylate alkyl ester and stir until homogeneous to obtain the final product.

[0046] An application of a medical adhesive for external wounds, used for skin surface protection during outdoor sports.

[0047] The outdoor activity in question is rock climbing.

[0048] Example 2

[0049] The specific implementation method is the same as in Example 1; the difference is that in Example 2, there are 100 parts of α-cyanoacrylate, 0.2 parts of polymerization inhibitor, 13 parts of plasticizer, and 8 parts of thickener.

[0050] Example 3

[0051] The specific implementation method is the same as in Example 1; the difference is that in Example 3, there are 100 parts of α-cyanoacrylate, 0.2 parts of polymerization inhibitor, 11 parts of plasticizer, and 10 parts of thickener.

[0052] Comparative Example 1

[0053] The specific implementation method is the same as in Example 1; the difference is that in Comparative Example 1, there are 100 parts of α-cyanoacrylate, 0.2 parts of polymerization inhibitor, 15 parts of plasticizer, and 6 parts of thickener.

[0054] Comparative Example 2

[0055] The specific implementation method is the same as in Example 1; the difference is that the weight ratio of diethyl adipate, diethylene glycol dibenzoate, and polyoxypropylene aryl ether in Comparative Example 2 is 1:0.3:0.8.

[0056] Comparative Example 3

[0057] The specific implementation method is the same as in Example 1; the difference is that the weight ratio of diethyl adipate, diethylene glycol dibenzoate, and polyoxypropylene aryl ether in Comparative Example 3 is 1:1:0.5.

[0058] Performance testing methods

[0059] Performance tests were conducted on the examples and comparative examples, and the test data are listed in Table 1.

[0060] 1. Polymerization time (solidification on tap water surface).

[0061] 2. Adhesion performance (i.e., lap-shear tensile strength and T-peel tensile bearing strength, tested according to the test methods in YY / T0729-2009).

[0062] Performance test data

[0063] Table 1

[0064]

Claims

1. A medical adhesive for external wound treatment, characterized in that, By weight, the components include: 80-120 parts of α-cyanoacrylate, 0.1-2 parts of polymerization inhibitor, 5-15 parts of plasticizer, and 3-12 parts of thickener; The plasticizer includes diethyl adipate, diethylene benzoate, and polyoxypropylene aryl ether, wherein the weight ratio of diethyl adipate, diethylene benzoate, and polyoxypropylene aryl ether is 1:(0.5-1):(1-1.8). The alkyl α-cyanoacrylate includes n-butyl α-cyanoacrylate and n-octyl α-cyanoacrylate, wherein the weight ratio of n-butyl α-cyanoacrylate to n-octyl α-cyanoacrylate is 2:(0.5-1.5).

2. The medical adhesive for external wounds according to claim 1, characterized in that, The weight ratio of α-butyl cyanoacrylate to α-octyl cyanoacrylate is 2:(0.7-1.4).

3. The medical adhesive for external wounds according to claim 1, characterized in that, The thickener includes at least one of methacrylate polymers, polyvinyl acetal, styrene copolymers, and nitrile rubber.

4. The medical adhesive for external wounds according to claim 3, characterized in that, The polymerization inhibitor includes at least one of sulfur dioxide, trifluoroacetic acid, and hydroquinone.

5. A medical adhesive for external wounds according to claim 1 or 4, characterized in that, The weight ratio of the plasticizer to the thickener is 1:(0.6-1.1).

6. The medical adhesive for external wounds according to claim 5, characterized in that, The weight ratio of the alkyl α-cyanoacrylate to the plasticizer is 20:(1-3).

7. A method for preparing medical adhesive for external wounds according to claim 1, characterized in that, Includes the following steps: Step 1: Mix the polymerization inhibitor, plasticizer, and thickener evenly and then sterilize to obtain a mixture; Step 2: Add the mixture obtained in Step 1 to α-cyanoacrylate and stir until homogeneous to obtain the final product.

8. The application of a method for preparing medical adhesive for external wounds according to claim 7, characterized in that, Preparation of skin surface protection products for outdoor sports.

Citation Information

Patent Citations

  • Method for preparing medical adhesive from alpha-alkyl cyanoacrylate monomer

    CN111714685A

  • Cyanoacrylate medical adhesive as well as preparation method and application thereof

    CN114796591A

  • Medical adhesive used for adhering skin and viscus hemostasis, and its prepn. method

    CN1692951A